I n the 1870s, an offshoot of New Haven’s Canal Street was renamed to honor the sprawling new factory that’d been built there. The complex was one of the biggest in the state, let alone the city, and by the late 19th century, the products its occupants made were world-renowned. By the early 20th century, the enterprise within its strong brick walls was the single-largest employer of New Haveners, and it was hugely profitable, too, netting an inflation-adjusted $28 million in the year 1900 alone.

It was the headquarters of the Winchester Repeating Arms Company, and the complex—half-abandoned, half-converted—still stands today, as do some of the other additions the Winchester family made to the city.

The creator of that dynasty, Oliver Fisher Winchester, had been a shirt manufacturer. But seeing the business possibilities of “repeating” rifles—“Probably it will modify the art of war; possibly it may revolutionize the whole science of war,” he once said of the technology that could allow soldiers to fire multiple rounds before reloading—he jockeyed for control of the local Volcanic Repeating Arms Company starting in 1855. On the bones of that enterprise, Winchester rebranded it the New Haven Repeating Arms Company—it wouldn’t be called Winchester until 1866—and doggedly sought to make it profitable.

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One of Winchester’s prospects was the federal government, a.k.a. the Union, during the Civil War. His sales pitch went something like this: “Where is the military genius that is to grasp this whole subject, and so modify the science of war as to best develop the capacities of this terrible engine—the exclusive control of which would enable any government (with resources sufficient to keep a half a million of men in the field) to rule the world?” Foregoing world domination, the government didn’t become a customer, but some of its soldiers took it upon themselves to buy Winchester’s superior rifles, which are credited in hindsight with leading the Union to victory in certain battles and inspiring fear throughout the Confederacy.

The company’s first major success was the “Henry” rifle, released in 1860. The Model 1866, named for the year it was released and nicknamed the “Yellow Boy” for its yellowish tinge, was the next to receive acclaim. But by far the most influential was the Model 1873, known as “the gun that won the West.” Along the way, the rifle became the favorite of frontiersmen, soldiers and those who romanticize them. In newspapers, magazines, books and—much later—movies and television, it became the Western genre’s weapon of choice, appearing in the hands of countless fictional cowboys and lawmen.

Less fictional, more local Winchester contributions have also survived the test of time, albeit in changed forms. New Haven City Hall (165 Church Street), built in 1861, boasted Oliver as one of the sponsors of its construction. The Winchester factory itself (275 Winchester Avenue), after falling into the sort of disrepair beloved by photographers, graffiti artists and urban explorers, has now been partially converted into luxury apartments. The Celentano Biotech, Health and Medical Magnet School (400 Canner Street) was once the Winchester Astronomical and Physical Observatory of Yale. Finished in 1882, it rivaled the best observatories of the age.

Following Oliver’s death in 1880 at the age of 70, his surviving family continued to change New Haven’s landscape. Since 1847, Yale had had a separate science institution, the Yale Scientific School, later renamed the Sheffield Scientific School. To its efforts, Jane Winchester, Oliver’s widow, donated $250,000 and a large hall, which stood where Becton Center on Prospect is today. Meanwhile, in 1901, the couple’s daughter, Hannah Jane, donated the Jane Ellen Hope Winchester Building (315 Cedar Street), which was used as Yale’s health clinic until 1960. Now, better known as the Hope Memorial Building, it serves as the Yale Medical School’s “major teaching facility,” according to YMS’s website.

One of the last large gifts the Winchester family made to the city was a tuberculosis hospital funded by Hannah’s sister-in-law, Sarah Winchester. Named for her husband, who died of the disease, the stately William Wirt Winchester Memorial Hospital, constructed in West Haven in 1918 on Campbell Avenue, is now the Veterans Administration Medical Center. But, over at Yale New Haven Hospital, the Winchester Chest Clinic carries on the underlying mission Sarah intended her hospital to pursue.

Sarah Winchester is a fascinating figure in her own right. The daughter of a craftsman and a member of a significant local lineage, she would endure a series of personal tragedies before becoming the subject of one of America’s most compelling ghost stories—a tale we’ll tell in tomorrow’s edition.

About Anne Ewbank

A California native and world traveler, Anne came to New Haven for graduate school and discovered that New England is as cold as everyone said it was. She loves reading books, playing guitar, exploring new towns and taking road trips but only as long as she gets to pick the music.